Does the CEO’s Executive Assistant Have a Lonelier Job Than the CEO?

I just had a meeting with a CEO and his assistant, who’ve returned to their office full time. The CEO expressed his gratitude for his assistant’s unwavering support. “I would have been lost without her. She understands that CEOs have a lonely job.” He was surprised when I said my experience indicates the CEO’s assistant has a lonelier job. As I talked, a light bulb seemed to go on for him. I noticed the sympathetic glances he was giving his long-time assistant. He kept nodding his head and muttering, “I never realized…you’re so right.”

During various stages of the pandemic, I’ve heard from CEOs’ assistants about being exhausted from taking care of everybody’s needs. None of these assistants asked for help from their employer. Particularly poignant was a conversation I had with an executive assistant who said that while other employees were being mentored and helped through a difficult period, she preferred not to talk to anyone in case it made her CEO look bad, as though he were insensitive to her needs. This woman’s comments are the classic “protect your executive” mindset of an executive assistant who understands that their job is to always showcase their executive in the best light.

Numerous surveys have been done and reports written about CEO loneliness. When Apple CEO Tim Cook said, “The adage that the CEO job is lonely is accurate in many ways,” it grabbed the headlines. But standing alongside the CEO and also experiencing loneliness and isolation—albeit without the direct burden of leadership and responsibility the CEO carries—is the CEO’s assistant.

During the lockdown, there were many articles written about how managers should reach out and help employees who were experiencing loneliness. CEOs and executives were advised how to handle the burden of their jobs while also dealing with their own feelings of isolation. Apart from my article for Chief Executive, I have not seen much focus on the person attending to the CEO, making certain they were meeting all their obligations to customers and employees. That person is routinely under the radar and, paradoxically, under the microscope.

A time-tested, elite executive assistant is not only the CEO’s face and voice to the world, they are also their eyes and ears. Because of this, people tend to avoid meaningful social connection with the CEO’s assistant, in case anything they say or do gets back to the CEO. Less-experienced assistants to CEOs encounter this distancing to a minor degree, but they are generally not considered as formidable as senior-level EAs, so their experience of separation is less intense. People are more inclined to engage with a less-experienced assistant, especially if they are fishing for information. That’s not something they would try with a seasoned executive assistant.

While the CEO and the EA both feel the isolation of their respective jobs, the assistant, more than the CEO, can never let their guard down. The CEO’s assistant must hold themselves to an elevated standard. Their conduct has to be beyond reproach. They have to remain slightly aloof, yet approachable, taking care that their relationships don’t compromise the discretion and confidentiality of their role. This automatically creates a distancing from certain employees who won’t let their guard down around the CEO’s assistant, even if the assistant is viewed as approachable, professional, courteous and trustworthy.

On the other hand, the CEO always has people who want to be near him/her and spend time with them. Their organizations will pay for the CEO to join peer leadership groups and go on luxury retreats with fellow CEOs they can confide in and learn from. If anything, CEOs may suffer from over-exposure because of all the people who vie to get close.

While both the CEO and their assistant may have few close allies or friends at work, it’s easier for the CEO to confide in their EA than the other way around. I know some assistants consider themselves particularly “pally” with their executive. Even if you have an enviable working relationship, it is the wise assistant who keeps just that slight distance between their executive and themselves—who let the CEO tell them all their inner-most thoughts, but who don’t share all of their own because it changes the dynamic of the relationship in subtle ways, and can put the EA at an unintended disadvantage. More than one assistant has seen an innocuous comment come back to haunt them when they were counting on their executive’s support.

Things happen in business—the chips are down, someone’s in a tight spot and confidences are inadvertently betrayed. The executive assistant must always have their executive’s back. It’s a cardinal rule, fundamental to the EA role and the only exception is if your executive is indulging in harmful or criminal activity. Otherwise, your discretion is absolute. However, whether the CEO has their assistant’s back can sometimes be a matter of expediency and self-preservation—for the executive and the organization. Assistants have got to get crystal clear about this. I’ve recently consulted with assistants who’ve suffered the consequences of expecting the trust factor to be unconditionally reciprocal. It’s then they realize just how alone in their job they are, and how vulnerable to capricious circumstances. It’s a gut-wrenching experience for them.

Few people comprehend the feeling of being separate that often permeates the life of a seasoned executive assistant to a CEO. They generally can’t confide in fellow employees about their professional challenges, or speak unreservedly at lunch-and-learns. They have to think twice about sharing even the slightest detail that may seem innocuous, but could be misconstrued or used in a compromising manner. The CEO’s assistant carries the weight of their job alone, and the discretion enforced on them by the job can cause them to be misunderstood.

In one job, I was executive assistant to the CEO/Chairman who owned the company. The company president and his assistant tried to keep me at arm’s length because the president felt I had more influence with the CEO than he did. With my eyes and ears everywhere, his assistant seemed nervous when I passed her desk, or requested routine business information. She and I had a cordial working relationship, but her executive encouraged her to be tight-lipped around me. In another job, I noticed my assistant would sit among colleagues at company functions, but I was always seated at the executives’ table. Once, when my CEO was delayed due to an emergency, he asked me to present his agenda items until he arrived. I let the directors know and proceeded to commence the meeting, when the director of sales asked if the CEO sent me to spy on them. Interestingly, my assistant was already in the room to take the minutes, but no such suspicion fell on her. Executive assistants to CEOs are viewed differently and held to a different standard.

Executive assistants who get promoted quickly notice the stakes are higher and the dynamic has shifted from when they were not supporting the CEO. As the CEO’s representative, you are now highly visible and you must expect your every move to be judged. The CEO can throw a tantrum, but not the executive assistant. The assistant must maintain their composure even in the most trying circumstances, or risk being branded temperamental and unsuited for the position.

EAs to CEOs are entrusted with information that they can’t share. If they go to lunch with other employees, they can’t complain about their boss. As one assistant remarked in my book, The CEO’s Secret Weapon, “Only my husband and my cat knew how I really felt.” CEOs are vital in shaping and influencing their company’s culture. Their executive assistants must consistently be ambassadors and exemplars of the cultural tone the executive wants to set. Because they often hold indirect power, the CEO’s assistant must be the epitome of discernment, impartiality and discretion, even if the executive has an occasional lapse. As Marshall Goldsmith commented in my book, “The way the assistant projects an air of proficiency, trust, poise, all reflect on the executive he or she is supporting.”

When I speak at events, I often hold a separate session for the CEO’s assistant, and for the small group of EAs who support their company’s highest level executives, so they have a chance to speak candidly with each other. Because of my experience in the role, these sessions are a welcome respite for the assistants who receive frank input from me—input and advice those who’ve never done that job could not comprehend. They can speak freely among their peers and be heard by colleagues who know exactly what they go through, without judgment or recrimination.

So the next time you turn to the CEO’s assistant with some obscure request no one else could possibly have the answer to, pass them in the hallway or see their face pop up on your screen, spare a thought for the load on their shoulders and the intensity of the demands on this person, who likely has the loneliest job in your company.

But whatever you do, don’t pity this prized thoroughbred, particularly if they’ve served at senior levels for a decade or more. By virtue of their position, many have unfettered access to the world’s movers and shakers. They are privy to exclusive conversations, deal-making, witnessing the inner workings of business at the highest and most confidential levels. They’ve seen and heard things you can’t imagine. They come and go through executive suites and high-stakes meetings without meriting a second glance, because they belong. They’ve developed their expertise by observing, supporting and playing confidant to masters of the game. They’re part of a select group of elite business professionals.

Lonely or not, they know who they are, they’re proud of what they do, are clear about what they signed up for, and take it all in stride, because that’s the way it is when you are your CEO’s Secret Weapon.

Jan Jones

Jan Jones is president of Jan Jones Worldwide, a bespoke speakers bureau that evolved from her industry experience as executive assistant to Tony Robbins, the world’s #1 life strategy expert, and ten years as exclusive representative for business visionary and author, Michael Gerber. Jan is the author of “The CEO’s Secret Weapon How Great Leaders and Their Assistants Maximize Productivity and Effectiveness

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